benzyl (R)-citronellyl 3-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate

Base Information

Chemical Name:benzyl (R)-citronellyl 3-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate
CAS No.:1352575-70-2
Molecular Formula:C₄₁H₆₂NO₉PSi
Molecular Weight:772.004
Hs Code.:

Synonyms:benzyl (R)-citronellyl 3-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate

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Chemical Property of benzyl (R)-citronellyl 3-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate

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Technology Process of benzyl (R)-citronellyl 3-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate

There total 8 articles about benzyl (R)-citronellyl 3-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 1117-61-9
(3R)-citronellol

: 1182275-48-4
benzyl 3-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate

: 1352575-70-2
benzyl (R)-citronellyl 3-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 16h; Inert atmosphere;
DOI:10.1039/c1ob06124k

Reference yield:

: 1182275-44-0
methyl 2-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)acetate

: 1352575-70-2
benzyl (R)-citronellyl 3-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: 1,4-diaza-bicyclo[2.2.2]octane / toluene / 7 h / Reflux; Inert atmosphere

2.2: DOWEX H⁺ (50WX₈-100) ion exchange resin / Inert atmosphere

3.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

With 1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; toluene; 3.1: Mitsunobu reaction;
DOI:10.1039/c1ob06124k

Reference yield:

: 1182275-42-8
3-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)prop-1-ene

: 1352575-70-2
benzyl (R)-citronellyl 3-(2-acetamido-4,6-O-(R)-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-α-D-glucopyranosyl)-2-oxopropylphosphonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: ozone; sodium hydroxide / methanol; dichloromethane / 3 h / -78 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: 1,4-diaza-bicyclo[2.2.2]octane / toluene / 7 h / Reflux; Inert atmosphere

3.2: DOWEX H⁺ (50WX₈-100) ion exchange resin / Inert atmosphere

4.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

With 1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium; di-isopropyl azodicarboxylate; ozone; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; toluene; 4.1: Mitsunobu reaction;
DOI:10.1039/c1ob06124k